


Drive

by littleladyyoda



Category: Succession (TV 2018)
Genre: Angst, Boss/Employee Relationship, F/M, Longing, Romance, Weddings, ive always wanted to break up a wedding, potentially questionable power dynamic, there may be eventual smut
Language: English
Status: In-Progress
Published: 2020-01-01
Updated: 2020-01-07
Packaged: 2021-02-27 07:20:14
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 2,155
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22073161
Author URL: https://archiveofourown.org/users/littleladyyoda/pseuds/littleladyyoda
Summary: Jess grabbed the train of her dress in both hands and walked as gracefully as she could down the back stairs.She knew who it was before she even stepped out the door.The developing relationship between Kendall Roy and his assistant, Jess.
Relationships: kendall roy/jess jordan
Comments: 1
Kudos: 41





	1. Chapter 1

“Jess, there’s a man here to see you. Says it’s urgent. Should I just tell him to go away?”

“No, no, I’ll go talk to him.”

Jess grabbed the train of her dress in both hands and walked as gracefully as she could down the back stairs.

She knew who it was before she even stepped out the door.

He was staring up at the sunset above the reception venue, but turned around when he heard her footsteps.

“Kendall.”

“You look beautiful, Jess,” he said.

“How did you…how are you…”

“It wasn’t too hard to find out,” he said. 

He was clad in jeans, a t-shirt, a black jacket, and sneakers instead of his usual suit, but goddamit if he didn’t look irresistible in whatever he was wearing. Jess willed away the traitorous thoughts of all the things she’d like to do to him and reminded herself that her fiancé was waiting.

“Are you in love with him?” Kendall asked, with that staggering bluntness she had grown to love about him.

“I care about him very much.”

“Not what I asked.”

“Love has many forms, Kendall.”

“Cut the bullshit, Jess. Tell me you’re in love with him and I’ll leave right now. You’ll never see me again.”

She sighed deeply.

“No, I’m not, Kendall. I’m not. But I want to build a life with someone I care about and it seems like the right move right now, ok? We’re good friends, he and I. We love each other and care for each other. 

“So I’m not going to be able to convince you to get in that car with me and ride off into the sunset?” he said, pointing at the black Escalade parked at the curb. 

She shook her head firmly.

“Well, then,” he said, a tight smile on his face and an edge of bitterness in his voice.

He leaned forward and kissed her gently on the cheek.

“Goodbye, Jess.”

Everything in her was screaming to go with him, to go after him. But she forced her feet up the stairs.


	2. Chapter 2

One Year Earlier:

Jess leaned against the radiator at the periphery of the room, rubbing her aching foot. She had tried to hide herself behind a large plant and hoped fervently that no one could see her. 

As with all Roy family gatherings, this one had an abundance of alcohol, pretentiousness, and snark. 

She peeked out from behind the plant and saw Logan dancing with Shiv, Greg taking an intern for a spin around the dance floor, and myriad other people in various stages of dancing that ran the gamut from bumping and grinding to waltzing. 

She was looking forward to a night of Netflix and pajamas when she could finally make her getaway. 

Looking up, she hastily shoved on her shoes as she saw Kendall walking toward her. 

“Is everything okay?” she asked, softly. “Do you need something?”

He held out his hand.

“I need you to dance with me.”

Jess shook her head a bit more firmly than necessary.

“Absolutely not. It’s not appropriate. People will talk, Kendall!”

Kendall let out a snort.

“Of course they won’t. I’m just taking my assistant for a spin around the dance floor. My dad used to dance with his secretary Monica every year before she retired.”

“Monica was like 100 years old! She could barely walk, let alone dance!”

Kendall kept his hand outstretched. He had that stubborn look in his eye that meant he wasn’t going away. 

“I’m not leaving until you dance with me, Jess.”

Jess grumbled under her breath, making sure her shoes were securely on her feet, and took his hand. 

He led her out from her hiding spot and into the middle of the dance floor, which coincided nicely with a slow song. 

He entwined his fingers with Jess’ and placed hand on her waist, as she lightly placed a hand on his shoulder.

They swayed for a moment or two before Kendall hissed in her ear.

“Let me lead!”

“I am letting you lead,” she hissed back, trying to keep a smile on her face.

She was terribly aware that all chatter in the room had stopped at that all eyes were on them. 

“No, you’re not.”

“Bossy,” Jess grumbled under her breath.

“I’d almost call that insubordination,” Kendall chuckled in her ear. 

Jess fought to keep her eyes anywhere but on Kendall, but she was vaguely aware that he was keeping his gaze only on her.

“You look nice tonight,” he said.

“Thank you,” she sniffed, trying desperately to ignore the deep timbre of his voice in her ear and the warmth emanating from his hands. “So do you.”

He had taken off his jacket and was wearing what she considered to be the best outfit he ever wore: dress pants and a slim-cut white shirt, slightly open at the neck, sleeves rolled up.

The song was a long one and she hated to admit how much she didn’t want it to end.

“They’re all looking at us, Kendall,” she whispered.

“I know.”

“Your dad is staring.”

“I’m aware.”

She growled softly in frustration. 

It was at that moment that Kendall gently dipped her. She grabbed onto his shoulders for support, but the surprise of the moment caused her to throw back her head and laugh in delight.

She was vaguely aware that a ripple went through the room. 

Kendall righted her, supporting her firmly. She knew he wouldn’t drop her and that thought, paired with the strength of his hands when he held her, made her stomach light up with butterflies. 

“I’m going to spin you,” he said.

“Kendall, no!” she said, giggling in spite of herself. 

“I’m gonna do it…wait for it…”

He gently twirled her and, despite knowing that she shouldn’t, that everyone was looking and that they were making snap judgments, she laughed again -- a genuinely happy sound.

“It’s good to see you laugh. I don’t get to see it often,” Kendall said.

They smiled at each other for a moment and she had the sudden urge to put her head against his shoulder, which she quickly suppressed. 

It was then that the song ended.

They were still staring at each other, gazes locked, when the chatter in the room resumed. 

As she looked into his brown eyes she had the terrifying realization that she’d worked for Kendall Roy for five years and had been in love with him for four and a half of those years. And, judging by the look on his face, he probably had similar feelings.

“I should go, of course. Oh my goodness, look at the time. Thank you for the dance. Lovely evening.” she babbled, tearing her gaze away and fleeing. 

She was halfway down the hallway when he caught up with her.

“Jess.”

She didn’t turn around, hoping he would go away.

“Jess, stop.”

His voice was commanding. It was the voice he used in conferences and meetings and it didn’t leave room for argument. 

“Jess. Please.”

Reluctantly, she turned around.

He jogged down the hallway towards her.

“You should definitely get back inside,” she said, softly. “People will wonder where you are.”

“Fuck them,” he said, decisively.

She rolled her eyes. 

“Where are you going,” he demanded. “There’s still two hours left of the party, at least. You can’t leave me alone with those people.”

“I’m going home, Kendall. To my cats and my pajamas and my glass of wine. My feet hurt and you just humiliated me in front of 100 people.”

The words came out sharper than she had intended. 

“But you seemed like you had fun,” he said, perplexed.

“I did,” she said, sighing. “I really, really did. And that’s the problem.”

“What problem? I don’t understand.”

She looked him dead in the eye.

“You’re Kendall Roy. You can do whatever the fuck you want. I’m just Jess Jordan, assistant. No one’s going to question you, judge you. But they’ll definitely do it to me.”

“I won’t let them,” he said, without hesitation.

“Kendall…”

He gently reached down, folding her fingers over and enveloping them in his hand. 

“You’re always safe with me, Jess,” he said, softly.

They stood like that for a moment.

“Why did you want to dance with me?” she asked, uncharacteristically bold.

“Because it occurred to me it might be my one and only chance,” he replied.

A small smile crossed her lips.

“I should go.”

Kendall didn’t let go of her hand.

“Only if I can come, too.”

She raised an eyebrow.

“You’re going to leave your fancy party with champagne and appetizers to come back to my shitty apartment and watch Real Housewives with me?”

“That’s what I was thinking, yes. As long as you're okay with it.”

“Well, then you should probably go get your coat,” she said, softly.

“Yes, ma’am.”


	3. Chapter 3

True to his word, Kendall watched “Real Housewives” with Jess without complaint.   
He settled himself onto the other end of the couch, occasional reaching over to grab a nacho from the plate she had set between them. Comfortable in his presence, she fell asleep after about two hours and was vaguely aware of him softly tucking a blanket around her before he slipped out the door.

Although they never discussed it, Kendall began to show up at her door most nights. He always had a pizza or some other offering in hand, which they would share as they worked their way through most of Jess’ Netflix queue. Kendall’s presence filled up her little apartment in a way she hadn’t previously been aware she was missing.   
They never addressed the events of the party, but on the nights that Kendall didn’t appear because of some family or business obligation, Jess would try and fail to ignore the blossoming ache in her chest. They were good friends and nothing more, she would sternly remind herself. 

They had a tacit understanding never to talk about work when they were alone. Aside from Kendall’s occasional comments about his family, they stuck to topics well removed from the Roy empire. Outside of work, Kendall was relaxed and happy. He seemed delighted to find that he could make Jess laugh – really laugh – her head thrown back, hands clasped together in mirth.

They continued this way for months. Jess was becoming uncomfortably aware that her friendship with Kendall, if it could be called that, was gradually amplifying her lack of a romantic relationship. She reminded herself that this wouldn’t last forever. That, one day, he’d meet someone who he would then start spending his evenings with. Plus, he was still her boss. Regardless of what they might share outside of work, there could never be anything between them. The Roys would see to that. 

After having this realization, Jess surprised herself by asking one of her friends to set her up on a date. It had been several years since she had been in a serious relationship and she was ready to fill her life with someone to whom she wasn’t simply a diversion to chase away loneliness.

The day of the date, she hoped fervently that nothing would happen that would keep her at the office past 5:00. To her pleasant surprise, she managed to make it to the end of the day with no fires to put out. 

She was halfway out the door when she saw Kendall walking towards her.

She groaned internally. She hadn’t told him about the date, instinctively knowing he wouldn’t like it. 

“Do you need something? If you don’t mind, I’m already late. First date. Don’t want to keep him waiting,” she rambled.

“First date,” Kendall said, stiffly. “Well, good luck. I hope he’s….nice.” 

“Kendall…”

“You’re late already. You should get going,” he said, the same stiff quality to his speech.

“And you’re clearly upset about something. So out with it,” said Jess, her exhaustion and irritation causing her to speak sharply.

“Ok, then,” Kendall said. “Quite frankly, I don’t think whoever this guy is, that he deserves you.”

“You’ve never even met him, Kendall.”

“I don’t have to. I just know.”

“Ok. And if I wanted to entertain that notion, what is your reasoning, exactly?”

“You deserve someone who’s going to give you everything. Someone who can take care of you. Someone who is so fucking in love with you it isn’t even funny.”

Jess opened her mouth and then closed it.

“Well, that’s very specific.”

“Yes, yes it is,” Kendall said, rather pointedly.

“Kendall,” she said softly. “I work for you. The optics…”

Kendall stepped forward, gently pulling her towards him, and rested his forehead against hers.

“Fuck the optics.”

“That can’t be your answer to everything, Ken. Eventually, we have to face the music on this.”

“Then let’s do that,” he said, taking her hand and staring down into her face.

“First you have to ask me not to go.”

“Don’t go,” he said, without hesitation.


End file.
